2-Chlorobenzothiazole → HCID 59351220, compound

HRID 2191969Notes

Reaction equation

HRID 2191969 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:2]1.Cl[C:22]1[S:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1>C(O)(C)C.C(=O)(O)[O-].[Na+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:8]([O:13][C:14]3[CH:20]=[CH:19][C:17]([NH:18][C:22]4[S:23][C:24]5[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=5[N:26]=4)=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:2]1

Participants

5

Reactant 2

HCID 119872-ChlorobenzothiazoleHCID 59351239HCID 59351239, compound

Product 1

HCID 59351220HCID 59351220, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

4-(3-(Tetrahydro-2H-pyran-3-yl)pyrazin-2-yloxy)aniline (0.082 g, 0.30 mmol) and 2-chlorobenzothiazole (0.039 mL, 0.30 mmol) were mixed in isopropyl alcohol (0.50 mL) in a microwave tube. The tube was sealed, and the reaction mixture was refluxed for 2.5 h. The reaction mixture was cooled to room temperature, diluted with sat. sodium bicarbonate, and extracted with EtOAc (2×). The combined organic layers were washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give N-(4-(3-(tetrahydro-2H-pyran-3-yl)pyrazin-2-yloxy)phenyl)benzo[d]thiazol-2-amine. MS (ESI, pos. ion) m/z: 405.1 (M+1). IC50 (uM) +++++.

Workup

  1. customThe tube was sealed
  2. temperaturethe reaction mixture was refluxed for 2.5 h
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic layers were washed with sat. sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d64741ea81734ea99a91b89af5448b37
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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